Hydrochloric Acid → 3-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-1,3-thiazol-2-ylbenzamide

HRID 20601Notes

Reaction equation

HRID 20601 reaction equation
Cl.[N:2]1([C:6]([C:8]2[CH:40]=[CH:39][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:38])[CH2:29][O:30][Si](C(C)(C)C)(C)C)[CH:26]=3)[C:16]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[O:17])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1.C(=O)(O)[O-].[Na+]>CO>[N:2]1([C:6]([C:8]2[CH:40]=[CH:39][C:11]([O:12][C:13]3[CH:14]=[C:15]([CH:24]=[C:25]([O:27][C@@H:28]([CH3:38])[CH2:29][OH:30])[CH:26]=3)[C:16]([NH:18][C:19]3[S:20][CH:21]=[CH:22][N:23]=3)=[O:17])=[CH:10][CH:9]=2)=[O:7])[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 593469213-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-1,3-thiazol-2-ylbenzamide

Product 1

HCID 115760793-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-hydroxy-1-methylethoxy]-N-1,3-thiazol-2-ylbenzamideYield 49.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% Hydrochloric acid (1 mL) was added to a solution of 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)-N-1,3-thiazol-2-ylbenzamide (284 mg, 0.5 mmol) in methanol (10 mL). The reaction was stirred at RT for 1 hour, saturated sodium bicarbonate solution added and the methanol evaporated. The aqueous residue was taken to pH 2 and extracted with ethyl acetate. The extracts were combined, washed with brine, dried (MgSO4), filtered, and evaporated in vacuo to give the crude product which was chromatographed on silica, eluting with 1% methanol in ethyl acetate, to give the desired compound (113 mg).

Workup

  1. customthe methanol evaporated
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give the crude product which
  8. customwas chromatographed on silica
  9. washeluting with 1% methanol in ethyl acetate

Sources & evidence

ORD record
ord-04faf9b9bc3641ff829492619ddf887d
Source dataset
uspto-grants-2010_06
Patent number
US07745475B2

Reaction notes

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